Sodium Bicarbonate → 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

HRID 2372217ノート

反応式

HRID 2372217 の反応式
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](C(Br)C)[N:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[CH:11]([CH3:12])[O:10][C:8](=[O:9])[C:7]=12

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 19902854Ethyl 4-chloro-2-(1-bromoethyl)nicotinate

生成物 1

HCID 199028524-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A mixture of ethyl 4-chloro-2-(1-bromoethyl)nicotinate (7.45 g) and sodium bicarbonate (4.00 g) in 50 ml of DMSO is heated at 120°, under nitrogen, for 2 hours, after which it is cooled, diluted with water, filtered and extracted with ether. The combined organic layers are washed with water and concentrated. The residue is taken into ethyl acetate, washed with brine, dried, concentrated and purified by flash chromatography to give 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one, which is then reacted with N-bromosuccinimide and 2,2'-azobis(2-methylpropionitrile), as above, to give 7-bromo-4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one.

後処理

  1. temperatureis heated at 120°, under nitrogen, for 2 hours
  2. temperatureafter which it is cooled
  3. filtrationfiltered
  4. extractionextracted with ether
  5. washThe combined organic layers are washed with water
  6. concentrationconcentrated
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated
  10. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-1c71f8c433a24b38bed0a32610856062
出典データセット
uspto-grants-1992_03
特許番号
US05098466

反応ノート

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